


D'yer Mak'er

by rotg5311



Category: Supernatural
Genre: Bi-Curious Dean Winchester, Castiel & Sam Winchester Friendship, Curious Jack Kline, M/M, Matchmaker Jack Kline, Uncomfortable Dean Winchester
Language: English
Status: In-Progress
Published: 2019-03-19
Updated: 2019-03-19
Packaged: 2019-11-24 10:21:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 2,033
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18163949
Author URL: https://archiveofourown.org/users/rotg5311/pseuds/rotg5311
Summary: In which Jack notices something between Dean and Cas and isn't sure why they aren't together.





	1. Chapter 1

The first time Jack called Dean out on his secret, Dean almost bit through his tongue. He had been chewing intently on his burger, not a care in the World, then Jack had asked. It was so jarring that instead of making up some decent excuse, Dean had just ended up yelling at Jack and changing the subject. It had been innocent enough, more of an observation than a question, but even then Dean could feel himself start to sweat. All jack had pointed out was that the couple on some stupid show he was watching, with Dean in the background not paying any attention to what it was about, had acted similar to Dean and Cas. He wasn’t even sure if Jack was capable of accusing him of anything, but the comment had hit too close to home when he looked at the screen and locked onto a pair of baby blue eyes.

After that, he was more cautious of what he said around Jack and how he acted. But as time went on, he could feel his plan backfiring. First it was a quirked eyebrow from Sam when all of them had been in a room together and Dean said something to Cas, emphasizing it’s ‘no homo’ meaning. Then it was Dean brushing up against Cas accidentally and jumping back, only to find Mary watching in on the whole interaction. But when he could see the disappointment on Cas’ face at the sudden change in their friendship, it started to wear on Dean.

He didn’t want to hurt Cas. In fact, the only thing he wanted to do was kiss a smile onto the man’s usually serious face. But Dean couldn’t, so he wouldn’t. Some things just weren’t meant to be, and this was one of them. Him and Cas. Dean had never been entirely comfortable at the attraction he felt to some men, so he never acted on it, and he wasn’t about to start that now. Besides, Cas was his best friend. Sure, sometimes he referred to Cas as being like a ‘brother’, but that was mostly to remind himself that no matter what he felt toward the Angel, he could never act on those feelings. So having Cas as a friend was better than nothing at all. He wouldn’t ruin anything by bringing up feelings that may or may not be returned. So when Jack started asking questions, Dean panicked.

The next time Jack brought it up was after Dean hung up with Cas. Cas had called to check in with them while out on a case with Sam. The two of them had started hanging out more and more and honestly Dean couldn’t be more happy. His two best friends finally getting along after so many years of a rocky relationship. Now, whenever the two of them went out together on the case, Cas would call and tell Dean every agonizingly embarrassing thing that happened to Sam. He had even been trying to get Cas to work the camera on his phone, because if Dean ever missed the opportunity to see Sam looking like Mr. Rogers again, he would rather die.

Except this time Cas got hurt. And Dean couldn’t help but fawn all over him. No one was there to hear the conversation. To hear the worry in Dean’s voice or the softness when he told Cas to feel better. Cas couldn’t heal himself the way he used to. Without Angels in Heaven, the few that were left were losing their powers. So Cas would be fine, it just might take him a couple hours. Then as he put the phone back on the table, Dean turned around to see Jack standing staring back at him.

“Jesus, Kid.” Dean jumped. He thought he had been alone, that’s the only reason he let himself be so...tender with Cas. “I should tie a bell to you.”

Jack ignored the comment. Either he didn’t get it or didn’t care to comment. “Was that Castiel?”

“Uh. Yeah.” Dean could feel the flush rising up in his cheeks. He had been caught red handed, even if he hadn't been doing other than letting his feelings show for just a few seconds.

“What happened to him?” Jack stood motionless in his strange Angel-like way. It had been one of the things he originally hated about Cas.

“Ran through with a machete. Just a small nick, really. He should be fine by the time they get back.” Dean recalled the short story to Jack, knowing full well that more had happened that Cas didn’t tell him.

“I can see why you would be worried about that.” Finally Jack sat down across the table from Dean. He wasn’t sure if that made things better or worse. He wasn’t even sure what to say in reply. Of course he was worried. Anyone that was friends with Cas would’ve been worried. If it had been Cas and Dean out and about, calling back to Sam, then Sam would’ve been worried about Cas too. But Dean was worried in a different way and he knew that’s what Jack was referring to.

“Yeah, well who wouldn’t be? I mean, come on. He’s an Angel but he’s not indestructible.”

Dean was trying to laugh off their conversation, but the way Jack’s face contorted with guilt made him pause. What was that about? More secrets. Of course. Why wouldn’t there be secrets between them? It made him angry, but he knew better than to ask about it. No one liked to be forthcoming about anything. He’d just wait for the truth to come out, it always did. Of course he knew it would be at the worst possible time, but that’s just how things were in their strange little makeshift family.


	2. Chapter 2

Jack left soon after that, conflicted with guilt. Dean’s comment on Castiel being indestructible brought up memories from what felt like ages ago. It brought up the time Jack had died and in order to keep the Empty from ripping him from Heaven into the great nothingness, Castiel had stepped up in his place. Offering up his life at the moment he finally becomes content. It was something that weighed heavily on Jack for the longest time. Sure, Castiel said he was fine, and that no one needed to know, because they would worry about it, but… it ate away at Jack. If Sam and Dean knew, maybe they could help. They would help. The two Brother’s had time and time again conned and scammed their way out of everything the universe threw at them. Jack knew Castiel’s last hope deal would be the same. So by promising not to say anything, Jack couldn’t help but feel like he was digging Castiel’s grave for him. In the metaphorical sense of course, because Hunter’s didn’t have graves, they got pyre’s.

Then they had done their whole deal with Jack and ‘losing his soul’, which, if he was being honest, all but thrust Castiel’s issue with the Empty out of his mind. But Jack was back at full power and operating on a small fraction of his soul, and everything was basically fine again. Of course, somet decisions took a little more thought and effort now, but Jack hadn’t done anything inherently ‘evil’ in months. Not since killing his snake. It had been an honest mistake. Jack knew about Heaven, afterall he had been, and he had heard Purgatory mentioned in passing, but he never put two and two together. Monster’s didn’t go to Heaven or Hell, they went to Purgatory when they died. So when Castiel told Sam and Dean what Jack had done and they all had a huge meltdown, he had to explain himself to them. Jack thought he was doing the right thing, so it came as an utter shock to learn that his mercy killing had been for nothing. He was only trying to help out. But the realization had been so upsetting that it made everyone realize Jack still possessed just a sliver of his soul. He apologized and spent a long time in his room replaying his actions over and over again in his head. Finally Sam had to come in with a full report on snakes to talk to Jack about. He told Jack that sometimes snakes stopped eating and starved to death anyways, no matter how hard people tried to stop it. He said he wasn’t sure if that would’ve happened to Jack’s snake, but it could have. Then they talked about killing, and how Jack should refrain from it until they could find out a way to fix his soullessness. Jack wasn’t sure how they would do it, just like he wasn’t sure how they would absolve Castiel’s deal with the Empty. He just knew that he trusted Sam and Dean and they would try their hardest to fix any problem for the people they cared about.

And still Jack felt empty. He was tired of being a burden. All he wanted was to help out. So when he started noticing some similar patterns from movies and shows with the way Dean and Castiel acted around each other, he knew what he had to do. It was clear they had feelings for each other, Jack even made sure to research love and its signs in depth first to triple check. Then came his plan. If he could get Dean and Castiel to admit their feelings for each other, then they would be together and happy. And the Empty would come for Castiel, leaving Sam and Dean to figure out how to stop it. It made sense to Jack the more he thought everything over. All he had to do was hope they could find a way to stop the Empty before it snatched Castiel, or find out how to bring him back once he was gone.

Jack figured Dean would be the easiest one to start with. If he started trying to wear Castiel down first, the Angel might fight back because of his promise to the Empty. If he wore Dean down first, then Jack figured Castiel wouldn’t be able to tell Dean no if he made a move first. Or that was the plan. Jack had zero experience on the fields of love, so he could only hope everything went according to plan. The only love he had ever felt was platonic. Sam, Dean, Castiel, all like Father’s to him. The memory of his Mother. Even Mary, Rowena, and some of the late Hunter’s had become like family to him. But even if he couldn’t relate to whatever feelings Dean and Castiel had for each other, Jack could still pick it out. In the way they looked at each other while the other looked away. Or when Dean casually flirted here and there with Castiel, always playing it off as a joke. Or how Castiel touched Dean in the most tender ways to heal him, when Jack knew the Angel’s healing factor was not touch-related. All of that and so, so much more was confirmation enough to set Jack into motion.

So the first time he tried, it went worse than planned. He had been expecting a few different reactions, but he hadn’t expected Dean to blow up in his face. Jack had always had a limited range of emotions before burning up most of his soul, but the intensity of Dean’s unexpected anger made him wonder if he might’ve cried at the pressure before.

All he had done was point out how the two characters on tv skirted around each other in the same manner Dean and Castiel did with each other. Two characters who had secret feelings for each other. After he told Dean that, the man broke down, had his little yelling fit, and left the room, Jack could barely even remember what Dean had been screaming about, because he had been too busy focusing on the panic that welled behind those green eyes. It left him feeling dejected, though he knew he couldn’t give up. Castiel and Dean were meant to be together, and Jack wouldn’t give up on trying to be their matchmaker.


End file.
